For sleep a wired pillow speaker works great, the advantage being there is nothing to fall out of your ears, and you can isolate the sound so only you hear it through the pillow: https://www.amazon.com/Crane-Company-PS2-SoftSpeaker-Speaker...

For airplanes, Bose or Sony both have noise-canceling wireless headphones in over-ear format with battery life over 18 hours. I wouldn't try to side-sleep in either one, but the relative quiet on aircraft is wonderful, especially if you find yourself on a turboprop.